# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_publ_contact_author_name        K.M.Muraleedharan
_publ_contact_author_email       mkm@iitm.ac.in
loop_
_publ_author_name
M.Ganesan
K.M.Muraleedharan
# end Validation Reply Form

# Attachment '- Compound 12e.cif'

#=====================================================================
data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 812794'
#TrackingRef '- Compound 12e.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H42 O8'
_chemical_formula_weight         506.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.474(3)
_cell_length_b                   12.149(7)
_cell_length_c                   21.524(11)
_cell_angle_alpha                82.90(3)
_cell_angle_beta                 86.90(3)
_cell_angle_gamma                89.09(3)
_cell_volume                     1418.2(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5543
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      22.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22200
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         24.18
_reflns_number_total             4498
_reflns_number_gt                2890
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1404P)^2^+0.1975P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.071(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4498
_refine_ls_number_parameters     343
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.1861
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1320(4) 0.3732(2) 0.38745(12) 0.0589(7) Uani 1 1 d . . .
C2 C 0.2034(4) 0.3982(2) 0.31652(12) 0.0605(7) Uani 1 1 d . . .
H2 H 0.3824 0.3991 0.3116 0.073 Uiso 1 1 calc R . .
C3 C 0.1096(5) 0.5194(2) 0.30188(12) 0.0612(7) Uani 1 1 d . . .
H3 H 0.2443 0.5673 0.2838 0.073 Uiso 1 1 calc R . .
C4 C 0.0368(5) 0.5459(2) 0.36757(12) 0.0624(7) Uani 1 1 d . . .
H4 H -0.0712 0.6109 0.3681 0.075 Uiso 1 1 calc R . .
C5 C 0.2604(5) 0.5524(2) 0.40461(12) 0.0626(7) Uani 1 1 d . . .
H5 H 0.3936 0.5912 0.3790 0.075 Uiso 1 1 calc R . .
C6 C 0.3248(5) 0.4274(2) 0.42255(12) 0.0618(7) Uani 1 1 d . . .
H6 H 0.4891 0.4111 0.4054 0.074 Uiso 1 1 calc R . .
C7 C 0.0677(5) 0.2561(2) 0.41264(15) 0.0760(9) Uani 1 1 d . . .
H7A H 0.0237 0.2508 0.4572 0.091 Uiso 1 1 calc R . .
H7B H -0.0699 0.2317 0.3914 0.091 Uiso 1 1 calc R . .
C8 C 0.2412(8) 0.0764(3) 0.4222(2) 0.1076(13) Uani 1 1 d . . .
H8A H 0.0894 0.0523 0.4071 0.129 Uiso 1 1 calc R . .
H8B H 0.2302 0.0641 0.4676 0.129 Uiso 1 1 calc R . .
C9 C 0.4497(8) 0.0103(3) 0.3980(2) 0.0981(12) Uani 1 1 d . . .
C10 C 0.5028(12) -0.0938(4) 0.4279(2) 0.1347(18) Uani 1 1 d . . .
H10 H 0.4092 -0.1219 0.4635 0.162 Uiso 1 1 calc R . .
C11 C 0.6911(14) -0.1563(4) 0.4059(3) 0.154(3) Uani 1 1 d . . .
H11 H 0.7234 -0.2266 0.4264 0.185 Uiso 1 1 calc R . .
C12 C 0.8302(13) -0.1163(4) 0.3546(3) 0.144(2) Uani 1 1 d . . .
H12 H 0.9590 -0.1587 0.3400 0.172 Uiso 1 1 calc R . .
C13 C 0.7814(10) -0.0136(4) 0.3241(2) 0.1265(16) Uani 1 1 d . . .
H13 H 0.8759 0.0139 0.2885 0.152 Uiso 1 1 calc R . .
C14 C 0.5918(8) 0.0491(3) 0.3462(2) 0.1004(12) Uani 1 1 d . . .
H14 H 0.5600 0.1191 0.3254 0.120 Uiso 1 1 calc R . .
C15 C 0.1120(5) 0.3153(3) 0.27604(14) 0.0727(8) Uani 1 1 d . . .
H15A H 0.1782 0.2423 0.2897 0.087 Uiso 1 1 calc R . .
H15B H -0.0650 0.3114 0.2808 0.087 Uiso 1 1 calc R . .
C16 C -0.1042(6) 0.5335(3) 0.25984(14) 0.0753(9) Uani 1 1 d . . .
H16A H -0.0581 0.5102 0.2193 0.090 Uiso 1 1 calc R . .
H16B H -0.2409 0.4890 0.2785 0.090 Uiso 1 1 calc R . .
C17 C 0.4106(6) 0.3189(3) 0.19183(15) 0.0792(9) Uani 1 1 d . . .
C18 C 0.4645(8) 0.3611(4) 0.12526(16) 0.1024(12) Uani 1 1 d . . .
H18A H 0.3229 0.3480 0.1021 0.123 Uiso 1 1 calc R . .
H18B H 0.4851 0.4408 0.1222 0.123 Uiso 1 1 calc R . .
C19 C 0.6771(8) 0.3146(4) 0.09481(18) 0.1141(13) Uani 1 1 d . . .
H19A H 0.6616 0.2346 0.0997 0.137 Uiso 1 1 calc R . .
H19B H 0.8208 0.3318 0.1162 0.137 Uiso 1 1 calc R . .
C20 C 0.7181(9) 0.3550(4) 0.02577(19) 0.1202(14) Uani 1 1 d . . .
H20A H 0.5722 0.3392 0.0050 0.144 Uiso 1 1 calc R . .
H20B H 0.7347 0.4350 0.0213 0.144 Uiso 1 1 calc R . .
C21 C 0.9230(12) 0.3106(6) -0.0068(3) 0.177(3) Uani 1 1 d . . .
H21A H 0.9048 0.2308 -0.0030 0.212 Uiso 1 1 calc R . .
H21B H 1.0687 0.3252 0.0145 0.212 Uiso 1 1 calc R . .
C22 C 0.9649(12) 0.3516(5) -0.0734(2) 0.165(2) Uani 1 1 d . . .
H22A H 1.1094 0.3170 -0.0897 0.248 Uiso 1 1 calc R . .
H22B H 0.9858 0.4305 -0.0782 0.248 Uiso 1 1 calc R . .
H22C H 0.8269 0.3340 -0.0959 0.248 Uiso 1 1 calc R . .
C23 C -0.3521(6) 0.6783(3) 0.21523(16) 0.0825(9) Uani 1 1 d D . .
O1 O -0.0776(3) 0.44397(16) 0.39522(8) 0.0669(6) Uani 1 1 d . . .
O2 O 0.3098(4) 0.39699(17) 0.48797(9) 0.0780(6) Uani 1 1 d . . .
H2A H 0.1968 0.3535 0.4973 0.117 Uiso 1 1 calc R . .
O3 O 0.1952(4) 0.60564(18) 0.45791(9) 0.0872(7) Uani 1 1 d . . .
H3A H 0.3158 0.6097 0.4785 0.131 Uiso 1 1 calc R . .
O4 O 0.2752(4) 0.19014(17) 0.40188(11) 0.0843(7) Uani 1 1 d . . .
O5 O 0.1848(4) 0.34720(18) 0.21126(9) 0.0811(7) Uani 1 1 d . . .
O6 O 0.5496(4) 0.2673(2) 0.22584(12) 0.1018(8) Uani 1 1 d . . .
O7 O -0.1705(4) 0.64840(19) 0.25292(10) 0.0892(7) Uani 1 1 d . A .
O8 O -0.4550(5) 0.6157(2) 0.18862(12) 0.0981(8) Uani 1 1 d . A .
C24 C -0.386(2) 0.8016(6) 0.2052(5) 0.108(3) Uani 0.612(11) 1 d PDU A 1
H24A H -0.4258 0.8263 0.2458 0.130 Uiso 0.612(11) 1 calc PR A 1
H24B H -0.2297 0.8340 0.1901 0.130 Uiso 0.612(11) 1 calc PR A 1
C25 C -0.570(3) 0.8477(10) 0.1624(6) 0.139(4) Uani 0.612(11) 1 d PDU A 1
H25A H -0.7065 0.7969 0.1647 0.167 Uiso 0.612(11) 1 calc PR A 1
H25B H -0.5002 0.8563 0.1198 0.167 Uiso 0.612(11) 1 calc PR A 1
C26 C -0.666(2) 0.9636(9) 0.1797(5) 0.151(3) Uani 0.612(11) 1 d PDU A 1
H26A H -0.7580 0.9540 0.2198 0.182 Uiso 0.612(11) 1 calc PR A 1
H26B H -0.5286 1.0116 0.1831 0.182 Uiso 0.612(11) 1 calc PR A 1
C27 C -0.832(3) 1.017(2) 0.1277(7) 0.264(6) Uani 0.612(11) 1 d PDU A 1
H27A H -0.9787 0.9730 0.1278 0.316 Uiso 0.612(11) 1 calc PR A 1
H27B H -0.8810 1.0909 0.1361 0.316 Uiso 0.612(11) 1 calc PR A 1
C28 C -0.697(4) 1.0230(16) 0.0635(6) 0.267(7) Uani 0.612(11) 1 d PDU A 1
H28A H -0.8024 1.0555 0.0319 0.401 Uiso 0.612(11) 1 calc PR A 1
H28B H -0.6494 0.9497 0.0551 0.401 Uiso 0.612(11) 1 calc PR A 1
H28C H -0.5537 1.0677 0.0632 0.401 Uiso 0.612(11) 1 calc PR A 1
C24' C -0.443(4) 0.7924(10) 0.2264(8) 0.108(3) Uani 0.388(11) 1 d PDU A 2
H24C H -0.5136 0.7869 0.2690 0.130 Uiso 0.388(11) 1 calc PR A 2
H24D H -0.3011 0.8398 0.2246 0.130 Uiso 0.388(11) 1 calc PR A 2
C25' C -0.622(4) 0.8502(16) 0.1852(10) 0.139(4) Uani 0.388(11) 1 d PDU A 2
H25C H -0.7747 0.8524 0.2103 0.167 Uiso 0.388(11) 1 calc PR A 2
H25D H -0.6500 0.8024 0.1534 0.167 Uiso 0.388(11) 1 calc PR A 2
C26' C -0.584(4) 0.9690(15) 0.1502(11) 0.151(3) Uani 0.388(11) 1 d PDU A 2
H26C H -0.4740 1.0066 0.1741 0.182 Uiso 0.388(11) 1 calc PR A 2
H26D H -0.4987 0.9610 0.1103 0.182 Uiso 0.388(11) 1 calc PR A 2
C27' C -0.804(5) 1.048(3) 0.1363(14) 0.264(6) Uani 0.388(11) 1 d PDU A 2
H27C H -0.9228 1.0462 0.1714 0.316 Uiso 0.388(11) 1 calc PR A 2
H27D H -0.7543 1.1236 0.1222 0.316 Uiso 0.388(11) 1 calc PR A 2
C28' C -0.890(6) 0.988(3) 0.0837(15) 0.267(7) Uani 0.388(11) 1 d PDU A 2
H28D H -1.0056 1.0344 0.0603 0.401 Uiso 0.388(11) 1 calc PR A 2
H28E H -0.9666 0.9200 0.1011 0.401 Uiso 0.388(11) 1 calc PR A 2
H28F H -0.7524 0.9727 0.0565 0.401 Uiso 0.388(11) 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0466(13) 0.0696(18) 0.0589(16) -0.0025(12) 0.0009(11) -0.0027(11)
C2 0.0495(14) 0.0719(18) 0.0597(16) -0.0085(13) 0.0008(11) -0.0037(12)
C3 0.0550(14) 0.0754(19) 0.0526(15) -0.0056(13) -0.0022(11) -0.0037(12)
C4 0.0547(15) 0.0765(19) 0.0540(16) -0.0034(13) 0.0010(12) 0.0081(13)
C5 0.0678(16) 0.0696(18) 0.0505(15) -0.0083(13) -0.0040(12) 0.0037(13)
C6 0.0546(14) 0.0751(19) 0.0545(16) -0.0040(13) -0.0020(11) 0.0003(12)
C7 0.0705(18) 0.076(2) 0.079(2) 0.0008(16) -0.0009(15) -0.0111(15)
C8 0.131(3) 0.073(2) 0.115(3) 0.013(2) -0.027(2) -0.022(2)
C9 0.135(3) 0.061(2) 0.101(3) -0.005(2) -0.044(3) 0.000(2)
C10 0.219(6) 0.068(3) 0.116(4) 0.002(2) -0.035(4) 0.002(3)
C11 0.265(8) 0.073(3) 0.132(5) -0.019(3) -0.071(5) 0.049(4)
C12 0.211(6) 0.095(4) 0.136(5) -0.045(3) -0.060(4) 0.053(4)
C13 0.178(5) 0.087(3) 0.118(3) -0.025(3) -0.025(3) 0.034(3)
C14 0.139(3) 0.066(2) 0.100(3) -0.011(2) -0.040(3) 0.011(2)
C15 0.0661(17) 0.085(2) 0.0698(19) -0.0175(15) -0.0069(13) -0.0023(14)
C16 0.0770(19) 0.084(2) 0.0655(19) -0.0050(15) -0.0168(14) 0.0055(15)
C17 0.078(2) 0.095(2) 0.068(2) -0.0207(17) -0.0103(16) 0.0064(17)
C18 0.123(3) 0.119(3) 0.066(2) -0.019(2) -0.003(2) 0.014(2)
C19 0.113(3) 0.144(4) 0.083(3) -0.012(2) 0.013(2) 0.006(3)
C20 0.130(3) 0.142(4) 0.090(3) -0.027(3) 0.010(2) -0.004(3)
C21 0.173(5) 0.234(7) 0.111(4) 0.006(4) 0.035(4) 0.037(5)
C22 0.190(6) 0.214(6) 0.090(3) -0.026(4) 0.025(3) -0.018(4)
C23 0.077(2) 0.100(3) 0.067(2) 0.0055(18) -0.0104(16) 0.0030(18)
O1 0.0454(9) 0.0888(14) 0.0624(12) 0.0022(10) 0.0072(8) 0.0026(9)
O2 0.0890(14) 0.0869(15) 0.0560(12) 0.0027(10) -0.0125(10) 0.0048(11)
O3 0.1190(17) 0.0849(15) 0.0620(13) -0.0220(11) -0.0201(11) 0.0189(12)
O4 0.0883(15) 0.0634(14) 0.0988(17) 0.0007(11) -0.0059(12) -0.0074(11)
O5 0.0828(14) 0.1015(16) 0.0629(13) -0.0233(11) -0.0126(10) 0.0116(11)
O6 0.0831(15) 0.139(2) 0.0816(16) -0.0066(14) -0.0062(12) 0.0214(14)
O7 0.0998(16) 0.0875(16) 0.0826(15) -0.0078(12) -0.0348(12) 0.0134(12)
O8 0.0871(16) 0.114(2) 0.0926(18) -0.0010(14) -0.0281(13) -0.0039(14)
C24 0.118(5) 0.106(3) 0.098(6) 0.002(3) -0.025(4) 0.012(3)
C25 0.129(6) 0.122(4) 0.167(7) -0.008(5) -0.042(5) 0.022(4)
C26 0.148(6) 0.135(4) 0.166(7) 0.001(5) -0.020(5) 0.040(4)
C27 0.259(8) 0.260(8) 0.273(8) -0.026(6) -0.041(6) -0.008(6)
C28 0.270(10) 0.263(9) 0.269(9) -0.022(6) -0.042(7) -0.002(7)
C24' 0.118(5) 0.106(3) 0.098(6) 0.002(3) -0.025(4) 0.012(3)
C25' 0.129(6) 0.122(4) 0.167(7) -0.008(5) -0.042(5) 0.022(4)
C26' 0.148(6) 0.135(4) 0.166(7) 0.001(5) -0.020(5) 0.040(4)
C27' 0.259(8) 0.260(8) 0.273(8) -0.026(6) -0.041(6) -0.008(6)
C28' 0.270(10) 0.263(9) 0.269(9) -0.022(6) -0.042(7) -0.002(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.438(3) . ?
C1 C7 1.498(4) . ?
C1 C6 1.533(4) . ?
C1 C2 1.549(4) . ?
C2 C15 1.518(4) . ?
C2 C3 1.552(4) . ?
C2 H2 0.9800 . ?
C3 C16 1.512(4) . ?
C3 C4 1.519(4) . ?
C3 H3 0.9800 . ?
C4 O1 1.443(3) . ?
C4 C5 1.505(4) . ?
C4 H4 0.9800 . ?
C5 O3 1.412(3) . ?
C5 C6 1.560(4) . ?
C5 H5 0.9800 . ?
C6 O2 1.409(3) . ?
C6 H6 0.9800 . ?
C7 O4 1.405(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O4 1.409(4) . ?
C8 C9 1.492(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.363(6) . ?
C9 C10 1.380(5) . ?
C10 C11 1.369(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.350(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O5 1.437(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O7 1.428(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O6 1.199(4) . ?
C17 O5 1.337(4) . ?
C17 C18 1.477(5) . ?
C18 C19 1.446(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.512(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.424(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.465(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O8 1.174(4) . ?
C23 O7 1.334(4) . ?
C23 C24 1.498(7) . ?
C23 C24' 1.508(9) . ?
O2 H2A 0.8200 . ?
O3 H3A 0.8200 . ?
C24 C25 1.463(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.575(9) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.553(9) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.525(10) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C24' C25' 1.471(9) . ?
C24' H24C 0.9700 . ?
C24' H24D 0.9700 . ?
C25' C26' 1.555(10) . ?
C25' H25C 0.9700 . ?
C25' H25D 0.9700 . ?
C26' C27' 1.543(10) . ?
C26' H26C 0.9700 . ?
C26' H26D 0.9700 . ?
C27' C28' 1.516(10) . ?
C27' H27C 0.9700 . ?
C27' H27D 0.9700 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C7 109.4(2) . . ?
O1 C1 C6 102.0(2) . . ?
C7 C1 C6 115.8(2) . . ?
O1 C1 C2 103.0(2) . . ?
C7 C1 C2 117.7(2) . . ?
C6 C1 C2 107.1(2) . . ?
C15 C2 C1 115.1(2) . . ?
C15 C2 C3 116.3(2) . . ?
C1 C2 C3 101.5(2) . . ?
C15 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C16 C3 C4 111.5(2) . . ?
C16 C3 C2 114.8(2) . . ?
C4 C3 C2 100.6(2) . . ?
C16 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
O1 C4 C5 103.8(2) . . ?
O1 C4 C3 101.7(2) . . ?
C5 C4 C3 110.3(2) . . ?
O1 C4 H4 113.4 . . ?
C5 C4 H4 113.4 . . ?
C3 C4 H4 113.4 . . ?
O3 C5 C4 108.6(2) . . ?
O3 C5 C6 111.9(2) . . ?
C4 C5 C6 101.9(2) . . ?
O3 C5 H5 111.3 . . ?
C4 C5 H5 111.3 . . ?
C6 C5 H5 111.3 . . ?
O2 C6 C1 114.2(2) . . ?
O2 C6 C5 111.9(2) . . ?
C1 C6 C5 100.4(2) . . ?
O2 C6 H6 110.0 . . ?
C1 C6 H6 110.0 . . ?
C5 C6 H6 110.0 . . ?
O4 C7 C1 107.1(2) . . ?
O4 C7 H7A 110.3 . . ?
C1 C7 H7A 110.3 . . ?
O4 C7 H7B 110.3 . . ?
C1 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
O4 C8 C9 110.1(3) . . ?
O4 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
O4 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C14 C9 C10 117.9(5) . . ?
C14 C9 C8 122.0(3) . . ?
C10 C9 C8 120.1(5) . . ?
C11 C10 C9 121.0(6) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.9(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.7(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 121.2(4) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
O5 C15 C2 110.5(2) . . ?
O5 C15 H15A 109.5 . . ?
C2 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O7 C16 C3 107.2(2) . . ?
O7 C16 H16A 110.3 . . ?
C3 C16 H16A 110.3 . . ?
O7 C16 H16B 110.3 . . ?
C3 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
O6 C17 O5 122.7(3) . . ?
O6 C17 C18 125.7(3) . . ?
O5 C17 C18 111.6(3) . . ?
C19 C18 C17 116.6(3) . . ?
C19 C18 H18A 108.1 . . ?
C17 C18 H18A 108.1 . . ?
C19 C18 H18B 108.1 . . ?
C17 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C18 C19 C20 115.1(4) . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 117.4(4) . . ?
C21 C20 H20A 107.9 . . ?
C19 C20 H20A 107.9 . . ?
C21 C20 H20B 107.9 . . ?
C19 C20 H20B 107.9 . . ?
H20A C20 H20B 107.2 . . ?
C20 C21 C22 117.3(5) . . ?
C20 C21 H21A 108.0 . . ?
C22 C21 H21A 108.0 . . ?
C20 C21 H21B 108.0 . . ?
C22 C21 H21B 108.0 . . ?
H21A C21 H21B 107.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O8 C23 O7 123.4(3) . . ?
O8 C23 C24 124.5(5) . . ?
O7 C23 C24 111.6(5) . . ?
O8 C23 C24' 125.6(8) . . ?
O7 C23 C24' 109.1(8) . . ?
C24 C23 C24' 20.7(10) . . ?
C1 O1 C4 96.57(18) . . ?
C6 O2 H2A 109.5 . . ?
C5 O3 H3A 109.5 . . ?
C7 O4 C8 113.8(3) . . ?
C17 O5 C15 117.4(2) . . ?
C23 O7 C16 116.2(3) . . ?
C25 C24 C23 118.1(8) . . ?
C25 C24 H24A 107.8 . . ?
C23 C24 H24A 107.8 . . ?
C25 C24 H24B 107.8 . . ?
C23 C24 H24B 107.8 . . ?
H24A C24 H24B 107.1 . . ?
C24 C25 C26 110.7(9) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C27 C26 C25 108.9(12) . . ?
C27 C26 H26A 109.9 . . ?
C25 C26 H26A 109.9 . . ?
C27 C26 H26B 109.9 . . ?
C25 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
C28 C27 C26 110.5(9) . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25' C24' C23 119.7(14) . . ?
C25' C24' H24C 107.4 . . ?
C23 C24' H24C 107.4 . . ?
C25' C24' H24D 107.4 . . ?
C23 C24' H24D 107.4 . . ?
H24C C24' H24D 106.9 . . ?
C24' C25' C26' 123.5(17) . . ?
C24' C25' H25C 106.5 . . ?
C26' C25' H25C 106.5 . . ?
C24' C25' H25D 106.5 . . ?
C26' C25' H25D 106.5 . . ?
H25C C25' H25D 106.5 . . ?
C27' C26' C25' 121(2) . . ?
C27' C26' H26C 107.1 . . ?
C25' C26' H26C 107.1 . . ?
C27' C26' H26D 107.1 . . ?
C25' C26' H26D 107.1 . . ?
H26C C26' H26D 106.8 . . ?
C28' C27' C26' 94.7(18) . . ?
C28' C27' H27C 112.8 . . ?
C26' C27' H27C 112.8 . . ?
C28' C27' H27D 112.8 . . ?
C26' C27' H27D 112.8 . . ?
H27C C27' H27D 110.2 . . ?
C27' C28' H28D 109.5 . . ?
C27' C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C27' C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C15 -98.4(3) . . . . ?
C7 C1 C2 C15 22.0(3) . . . . ?
C6 C1 C2 C15 154.4(2) . . . . ?
O1 C1 C2 C3 28.1(2) . . . . ?
C7 C1 C2 C3 148.5(2) . . . . ?
C6 C1 C2 C3 -79.1(2) . . . . ?
C15 C2 C3 C16 13.6(3) . . . . ?
C1 C2 C3 C16 -112.2(2) . . . . ?
C15 C2 C3 C4 133.3(2) . . . . ?
C1 C2 C3 C4 7.6(2) . . . . ?
C16 C3 C4 O1 81.0(3) . . . . ?
C2 C3 C4 O1 -41.0(2) . . . . ?
C16 C3 C4 C5 -169.3(2) . . . . ?
C2 C3 C4 C5 68.6(3) . . . . ?
O1 C4 C5 O3 -87.5(3) . . . . ?
C3 C4 C5 O3 164.3(2) . . . . ?
O1 C4 C5 C6 30.8(2) . . . . ?
C3 C4 C5 C6 -77.5(3) . . . . ?
O1 C1 C6 O2 82.2(3) . . . . ?
C7 C1 C6 O2 -36.5(3) . . . . ?
C2 C1 C6 O2 -170.0(2) . . . . ?
O1 C1 C6 C5 -37.6(2) . . . . ?
C7 C1 C6 C5 -156.3(2) . . . . ?
C2 C1 C6 C5 70.2(2) . . . . ?
O3 C5 C6 O2 -1.7(3) . . . . ?
C4 C5 C6 O2 -117.5(2) . . . . ?
O3 C5 C6 C1 119.8(2) . . . . ?
C4 C5 C6 C1 4.0(2) . . . . ?
O1 C1 C7 O4 177.9(2) . . . . ?
C6 C1 C7 O4 -67.5(3) . . . . ?
C2 C1 C7 O4 60.9(3) . . . . ?
O4 C8 C9 C14 -23.1(5) . . . . ?
O4 C8 C9 C10 157.4(4) . . . . ?
C14 C9 C10 C11 -0.4(7) . . . . ?
C8 C9 C10 C11 179.1(5) . . . . ?
C9 C10 C11 C12 0.6(9) . . . . ?
C10 C11 C12 C13 -0.7(9) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C10 C9 C14 C13 0.3(6) . . . . ?
C8 C9 C14 C13 -179.2(4) . . . . ?
C12 C13 C14 C9 -0.4(7) . . . . ?
C1 C2 C15 O5 179.1(2) . . . . ?
C3 C2 C15 O5 60.5(3) . . . . ?
C4 C3 C16 O7 64.8(3) . . . . ?
C2 C3 C16 O7 178.3(2) . . . . ?
O6 C17 C18 C19 15.7(6) . . . . ?
O5 C17 C18 C19 -165.8(4) . . . . ?
C17 C18 C19 C20 176.6(4) . . . . ?
C18 C19 C20 C21 -179.1(5) . . . . ?
C19 C20 C21 C22 -178.9(6) . . . . ?
C7 C1 O1 C4 -179.7(2) . . . . ?
C6 C1 O1 C4 57.2(2) . . . . ?
C2 C1 O1 C4 -53.8(2) . . . . ?
C5 C4 O1 C1 -54.9(2) . . . . ?
C3 C4 O1 C1 59.6(2) . . . . ?
C1 C7 O4 C8 -178.9(3) . . . . ?
C9 C8 O4 C7 168.9(3) . . . . ?
O6 C17 O5 C15 1.1(5) . . . . ?
C18 C17 O5 C15 -177.5(3) . . . . ?
C2 C15 O5 C17 82.9(3) . . . . ?
O8 C23 O7 C16 0.0(5) . . . . ?
C24 C23 O7 C16 -173.1(5) . . . . ?
C24' C23 O7 C16 165.0(9) . . . . ?
C3 C16 O7 C23 177.7(2) . . . . ?
O8 C23 C24 C25 4.0(12) . . . . ?
O7 C23 C24 C25 177.0(8) . . . . ?
C24' C23 C24 C25 -96(3) . . . . ?
C23 C24 C25 C26 154.2(13) . . . . ?
C24 C25 C26 C27 171.9(12) . . . . ?
C25 C26 C27 C28 -55(2) . . . . ?
O8 C23 C24' C25' -23(2) . . . . ?
O7 C23 C24' C25' 172.4(15) . . . . ?
C24 C23 C24' C25' 72(3) . . . . ?
C23 C24' C25' C26' -126(3) . . . . ?
C24' C25' C26' C27' -149(2) . . . . ?
C25' C26' C27' C28' -75(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.82 2.37 2.940(4) 126.8 2_566
O3 H3A O2 0.82 2.21 3.005(3) 164.6 2_666

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        24.18
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.141
_vrf_PLAT242_shelxl              
;
PROBLEM: Check Low Ueq as Compared to Neighbors for C26
RESPONSE: This may be attributed to the severe disorder of the
terminal group along with large libration of that region.
;
# end Validation Reply Form


data_new
_database_code_depnum_ccdc_archive 'CCDC 846065'
#TrackingRef '- Compound (-)3c.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C18 H32 O6'

_chemical_formula_sum            'C18 H32 O6'

_chemical_formula_weight         344.44

_chemical_absolute_configuration .

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source

C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)

loop_

_symmetry_equiv_pos_as_xyz

'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.5386(5)

_cell_length_b                   7.0291(7)

_cell_length_c                   23.255(2)

_cell_angle_alpha                90.00

_cell_angle_beta                 93.015(5)

_cell_angle_gamma                90.00

_cell_volume                     904.10(15)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    2080

_cell_measurement_theta_min      2.63

_cell_measurement_theta_max      23.83

_exptl_crystal_description       Block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.22

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.265

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             376

_exptl_absorpt_coefficient_mu    0.093

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9681

_exptl_absorpt_correction_T_max  0.9861

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruler APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            7136

_diffrn_reflns_av_R_equivalents  0.0287

_diffrn_reflns_av_sigmaI/netI    0.0681

_diffrn_reflns_limit_h_min       -5

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -32

_diffrn_reflns_limit_l_max       32

_diffrn_reflns_theta_min         0.88

_diffrn_reflns_theta_max         30.65

_reflns_number_total             4128

_reflns_number_gt                2435

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       APEXII,Bruker,2004

_computing_cell_refinement       APEXII,Bruker,2004

_computing_data_reduction        SAINT,Bruker,2004

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'

_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.055(5)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.7(13)

_refine_ls_number_reflns         4128

_refine_ls_number_parameters     231

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.1089

_refine_ls_R_factor_gt           0.0496

_refine_ls_wR_factor_ref         0.1346

_refine_ls_wR_factor_gt          0.0990

_refine_ls_goodness_of_fit_ref   1.033

_refine_ls_restrained_S_all      1.033

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

C1 C 0.2546(5) 0.1619(4) 0.39707(12) 0.0332(7) Uani 1 1 d . . .
H1 H 0.3758 0.2164 0.4245 0.040 Uiso 1 1 calc R . .
C2 C 0.1547(5) -0.0225(4) 0.42208(12) 0.0297(6) Uani 1 1 d . . .
H2 H 0.0150 -0.0007 0.4454 0.036 Uiso 1 1 calc R . .
C3 C 0.3510(5) -0.1394(4) 0.45314(12) 0.0338(7) Uani 1 1 d . . .
H3 H 0.4536 -0.0580 0.4784 0.041 Uiso 1 1 calc R . .
C4 C 0.4953(5) -0.2114(4) 0.40099(13) 0.0348(7) Uani 1 1 d . . .
H4 H 0.6574 -0.1552 0.4018 0.042 Uiso 1 1 calc R . .
C5 C 0.3382(5) -0.1331(4) 0.35100(12) 0.0335(7) Uani 1 1 d . . .
H5 H 0.3526 -0.2049 0.3152 0.040 Uiso 1 1 calc R . .
C6 C 0.3835(5) 0.0804(4) 0.34414(11) 0.0356(7) Uani 1 1 d . . .
H6 H 0.5574 0.1057 0.3489 0.043 Uiso 1 1 calc R . .
C7 C 0.0615(6) 0.3094(4) 0.38230(13) 0.0384(7) Uani 1 1 d . . .
H7A H 0.1268 0.4041 0.3571 0.046 Uiso 1 1 calc R . .
H7B H -0.0735 0.2481 0.3615 0.046 Uiso 1 1 calc R . .
C8 C 0.2886(6) 0.1536(5) 0.28620(12) 0.0491(9) Uani 1 1 d . . .
H8A H 0.1269 0.1055 0.2771 0.059 Uiso 1 1 calc R . .
H8B H 0.2831 0.2916 0.2862 0.059 Uiso 1 1 calc R . .
C9 C 0.3948(6) 0.1275(4) 0.18958(13) 0.0399(8) Uani 1 1 d . . .
C10 C 0.5842(6) 0.0697(5) 0.15026(12) 0.0388(7) Uani 1 1 d . . .
H10A H 0.5922 -0.0681 0.1494 0.047 Uiso 1 1 calc R . .
H10B H 0.7393 0.1161 0.1657 0.047 Uiso 1 1 calc R . .
C11 C 0.5441(6) 0.1414(4) 0.08944(12) 0.0391(7) Uani 1 1 d . . .
H11A H 0.5396 0.2794 0.0900 0.047 Uiso 1 1 calc R . .
H11B H 0.3882 0.0968 0.0740 0.047 Uiso 1 1 calc R . .
C12 C 0.7380(6) 0.0773(5) 0.05011(12) 0.0390(7) Uani 1 1 d . . .
H12A H 0.8936 0.1208 0.0661 0.047 Uiso 1 1 calc R . .
H12B H 0.7415 -0.0607 0.0497 0.047 Uiso 1 1 calc R . .
C13 C 0.7051(6) 0.1474(4) -0.01109(12) 0.0385(7) Uani 1 1 d . . .
H13A H 0.5493 0.1043 -0.0271 0.046 Uiso 1 1 calc R . .
H13B H 0.7027 0.2854 -0.0108 0.046 Uiso 1 1 calc R . .
C14 C 0.8982(5) 0.0820(5) -0.04994(12) 0.0385(7) Uani 1 1 d . . .
H14A H 0.8990 -0.0560 -0.0506 0.046 Uiso 1 1 calc R . .
H14B H 1.0541 0.1234 -0.0335 0.046 Uiso 1 1 calc R . .
C15 C 0.8699(6) 0.1534(4) -0.11138(12) 0.0402(7) Uani 1 1 d . . .
H15A H 0.7170 0.1077 -0.1284 0.048 Uiso 1 1 calc R . .
H15B H 0.8628 0.2913 -0.1108 0.048 Uiso 1 1 calc R . .
C16 C 1.0697(5) 0.0933(5) -0.14933(12) 0.0385(7) Uani 1 1 d . . .
H16A H 1.0838 -0.0443 -0.1481 0.046 Uiso 1 1 calc R . .
H16B H 1.2213 0.1460 -0.1338 0.046 Uiso 1 1 calc R . .
C17 C 1.0318(6) 0.1548(5) -0.21146(13) 0.0487(9) Uani 1 1 d . . .
H17A H 0.8787 0.1042 -0.2268 0.058 Uiso 1 1 calc R . .
H17B H 1.0212 0.2925 -0.2128 0.058 Uiso 1 1 calc R . .
C18 C 1.2278(8) 0.0914(8) -0.24923(15) 0.0760(12) Uani 1 1 d . . .
H18A H 1.3804 0.1403 -0.2344 0.114 Uiso 1 1 calc R . .
H18B H 1.1947 0.1384 -0.2876 0.114 Uiso 1 1 calc R . .
H18C H 1.2338 -0.0451 -0.2499 0.114 Uiso 1 1 calc R . .
O1 O 0.0970(3) -0.1367(3) 0.37195(8) 0.0327(5) Uani 1 1 d . . .
O2 O 0.2535(4) -0.2912(3) 0.48516(9) 0.0409(5) Uani 1 1 d . . .
O3 O 0.5080(5) -0.4120(3) 0.39895(11) 0.0496(6) Uani 1 1 d . . .
O4 O -0.0241(4) 0.4023(3) 0.43194(10) 0.0458(6) Uani 1 1 d . . .
O5 O 0.4542(4) 0.0859(4) 0.24467(8) 0.0509(6) Uani 1 1 d . . .
O6 O 0.2079(5) 0.2024(5) 0.17538(10) 0.0757(9) Uani 1 1 d . . .
H4O H -0.093(7) 0.315(6) 0.4503(16) 0.068(13) Uiso 1 1 d . . .
H2O H 0.193(8) -0.387(7) 0.4619(19) 0.094(14) Uiso 1 1 d . . .
H3O H 0.631(9) -0.446(7) 0.410(2) 0.10(2) Uiso 1 1 d . . .

loop_

_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12

C1 0.0394(19) 0.0291(15) 0.0310(15) 0.0002(12) 0.0013(13) -0.0036(12)
C2 0.0322(18) 0.0303(14) 0.0269(15) -0.0031(11) 0.0055(12) -0.0020(12)
C3 0.0397(18) 0.0299(14) 0.0317(15) 0.0007(12) 0.0021(13) -0.0069(13)
C4 0.0291(18) 0.0343(15) 0.0417(18) 0.0024(13) 0.0066(14) 0.0005(12)
C5 0.0328(17) 0.0356(15) 0.0330(15) -0.0045(13) 0.0085(13) 0.0007(13)
C6 0.0341(17) 0.0365(14) 0.0364(16) 0.0048(14) 0.0050(13) -0.0002(13)
C7 0.050(2) 0.0311(16) 0.0344(16) 0.0015(12) 0.0067(14) 0.0031(13)
C8 0.060(2) 0.053(2) 0.0368(17) 0.0102(15) 0.0186(16) 0.0182(16)
C9 0.048(2) 0.0365(18) 0.0359(17) 0.0069(13) 0.0089(15) 0.0088(14)
C10 0.0379(18) 0.0399(16) 0.0393(17) 0.0045(14) 0.0079(14) 0.0096(14)
C11 0.044(2) 0.0355(17) 0.0376(16) 0.0026(12) 0.0055(14) 0.0056(13)
C12 0.0426(19) 0.0367(15) 0.0382(16) 0.0029(14) 0.0067(14) 0.0029(14)
C13 0.0404(19) 0.0392(17) 0.0361(15) 0.0001(13) 0.0042(13) 0.0014(12)
C14 0.043(2) 0.0338(14) 0.0388(16) 0.0009(14) 0.0060(14) -0.0029(14)
C15 0.0373(19) 0.0428(18) 0.0409(17) 0.0012(13) 0.0056(14) 0.0017(13)
C16 0.0372(18) 0.0392(15) 0.0394(16) 0.0007(14) 0.0040(13) -0.0043(14)
C17 0.051(2) 0.054(2) 0.0415(18) -0.0035(15) 0.0067(16) -0.0083(15)
C18 0.074(3) 0.107(3) 0.048(2) -0.002(2) 0.018(2) -0.010(3)
O1 0.0303(11) 0.0356(10) 0.0324(10) -0.0056(8) 0.0034(8) -0.0042(8)
O2 0.0570(15) 0.0309(11) 0.0354(11) 0.0019(10) 0.0093(10) -0.0028(10)
O3 0.0531(18) 0.0324(11) 0.0646(16) 0.0030(12) 0.0156(13) 0.0090(11)
O4 0.0627(16) 0.0299(11) 0.0465(13) -0.0009(10) 0.0197(12) 0.0000(10)
O5 0.0544(15) 0.0638(14) 0.0362(12) 0.0129(11) 0.0167(10) 0.0208(12)
O6 0.070(2) 0.113(2) 0.0450(14) 0.0119(16) 0.0107(13) 0.0472(18)

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

;

loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag

C1 C7 1.516(4) . ?
C1 C2 1.536(4) . ?
C1 C6 1.564(4) . ?
C1 H1 0.9800 . ?
C2 O1 1.438(3) . ?
C2 C3 1.515(4) . ?
C2 H2 0.9800 . ?
C3 O2 1.424(3) . ?
C3 C4 1.571(4) . ?
C3 H3 0.9800 . ?
C4 O3 1.413(3) . ?
C4 C5 1.518(4) . ?
C4 H4 0.9800 . ?
C5 O1 1.446(3) . ?
C5 C6 1.532(4) . ?
C5 H5 0.9800 . ?
C6 C8 1.511(4) . ?
C6 H6 0.9800 . ?
C7 O4 1.429(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O5 1.447(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O6 1.192(4) . ?
C9 O5 1.338(4) . ?
C9 C10 1.484(4) . ?
C10 C11 1.507(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.516(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.508(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.508(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.515(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.512(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.512(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.500(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O2 H2O 0.92(5) . ?
O3 H3O 0.76(5) . ?
O4 H4O 0.85(4) . ?

loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag

C7 C1 C2 113.5(2) . . ?
C7 C1 C6 114.7(2) . . ?
C2 C1 C6 100.2(2) . . ?
C7 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
C6 C1 H1 109.3 . . ?
O1 C2 C3 102.0(2) . . ?
O1 C2 C1 103.5(2) . . ?
C3 C2 C1 112.0(2) . . ?
O1 C2 H2 112.8 . . ?
C3 C2 H2 112.8 . . ?
C1 C2 H2 112.8 . . ?
O2 C3 C2 111.9(2) . . ?
O2 C3 C4 112.6(2) . . ?
C2 C3 C4 100.8(2) . . ?
O2 C3 H3 110.4 . . ?
C2 C3 H3 110.4 . . ?
C4 C3 H3 110.4 . . ?
O3 C4 C5 111.3(3) . . ?
O3 C4 C3 112.1(2) . . ?
C5 C4 C3 100.4(2) . . ?
O3 C4 H4 110.9 . . ?
C5 C4 H4 110.9 . . ?
C3 C4 H4 110.9 . . ?
O1 C5 C4 103.8(2) . . ?
O1 C5 C6 102.2(2) . . ?
C4 C5 C6 110.2(2) . . ?
O1 C5 H5 113.3 . . ?
C4 C5 H5 113.3 . . ?
C6 C5 H5 113.3 . . ?
C8 C6 C5 112.1(3) . . ?
C8 C6 C1 115.2(2) . . ?
C5 C6 C1 101.1(2) . . ?
C8 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C1 C6 H6 109.4 . . ?
O4 C7 C1 113.0(2) . . ?
O4 C7 H7A 109.0 . . ?
C1 C7 H7A 109.0 . . ?
O4 C7 H7B 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O5 C8 C6 106.3(2) . . ?
O5 C8 H8A 110.5 . . ?
C6 C8 H8A 110.5 . . ?
O5 C8 H8B 110.5 . . ?
C6 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
O6 C9 O5 121.8(3) . . ?
O6 C9 C10 125.6(3) . . ?
O5 C9 C10 112.6(3) . . ?
C9 C10 C11 114.4(3) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 113.1(2) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 114.7(2) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 114.3(3) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 115.0(2) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C14 114.5(2) . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 114.1(3) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 114.0(3) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 O1 C5 95.37(19) . . ?
C3 O2 H2O 112(3) . . ?
C4 O3 H3O 111(4) . . ?
C7 O4 H4O 104(2) . . ?
C9 O5 C8 115.8(2) . . ?

loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag

C7 C1 C2 O1 88.8(3) . . . . ?
C6 C1 C2 O1 -34.0(3) . . . . ?
C7 C1 C2 C3 -162.2(2) . . . . ?
C6 C1 C2 C3 75.1(3) . . . . ?
O1 C2 C3 O2 -80.7(3) . . . . ?
C1 C2 C3 O2 169.2(2) . . . . ?
O1 C2 C3 C4 39.2(2) . . . . ?
C1 C2 C3 C4 -70.8(3) . . . . ?
O2 C3 C4 O3 -3.1(4) . . . . ?
C2 C3 C4 O3 -122.6(3) . . . . ?
O2 C3 C4 C5 115.1(2) . . . . ?
C2 C3 C4 C5 -4.3(3) . . . . ?
O3 C4 C5 O1 87.2(3) . . . . ?
C3 C4 C5 O1 -31.6(3) . . . . ?
O3 C4 C5 C6 -164.0(2) . . . . ?
C3 C4 C5 C6 77.2(3) . . . . ?
O1 C5 C6 C8 -86.4(3) . . . . ?
C4 C5 C6 C8 163.8(2) . . . . ?
O1 C5 C6 C1 36.8(3) . . . . ?
C4 C5 C6 C1 -73.0(3) . . . . ?
C7 C1 C6 C8 -2.8(4) . . . . ?
C2 C1 C6 C8 119.2(3) . . . . ?
C7 C1 C6 C5 -123.8(3) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C2 C1 C7 O4 75.1(3) . . . . ?
C6 C1 C7 O4 -170.5(2) . . . . ?
C5 C6 C8 O5 -74.0(3) . . . . ?
C1 C6 C8 O5 171.1(3) . . . . ?
O6 C9 C10 C11 9.6(5) . . . . ?
O5 C9 C10 C11 -170.7(3) . . . . ?
C9 C10 C11 C12 -179.0(3) . . . . ?
C10 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C12 C13 C14 C15 -179.2(3) . . . . ?
C13 C14 C15 C16 177.7(3) . . . . ?
C14 C15 C16 C17 176.4(3) . . . . ?
C15 C16 C17 C18 -178.8(3) . . . . ?
C3 C2 O1 C5 -59.0(2) . . . . ?
C1 C2 O1 C5 57.4(2) . . . . ?
C4 C5 O1 C2 56.4(2) . . . . ?
C6 C5 O1 C2 -58.2(2) . . . . ?
O6 C9 O5 C8 -5.7(5) . . . . ?
C10 C9 O5 C8 174.6(3) . . . . ?
C6 C8 O5 C9 176.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.851

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.931

_refine_diff_density_max         0.390

_refine_diff_density_min         -0.262

_refine_diff_density_rms         0.095

_vrf_PLAT029_new                 
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.931
RESPONSE: Even though crystal data was collected up to 0.73 \%A
resolution, the crystal (the largest available) still
diffracted quite weakly at high angle. On repeated recrystallisation
we could get only small sized crystals.

;